✦ LIBER ✦
AnomericO-alkylation, 11. AnomericO-Alkylation ofO-Unprotected Hexoses and Pentoses – Convenient Synthesis of Decyl, Benzyl, and Allyl Glycosides
✍ Scribed by Klotz, Wolfgang ;Schmidt, Richard R.
- Publisher
- John Wiley and Sons
- Year
- 1993
- Tongue
- English
- Weight
- 797 KB
- Volume
- 1993
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
The base‐promoted reaction of O‐unprotected aldoses 1–6 with didecyl sulfate in DMPU affords decyl glycosides 1aα–6aα and 1aβ, 3aβ–6aβ in good overall yields. Similarly, the treatment of O‐unprotected hexoses 1–4 and pentoses 5 and 6 with benzyl bromide and allyl bromide yields after subsequent O‐acetylation monosaccharides 1cα–6cα, 1cβ, 3cβ–6cβ and 1dα–6dα, 1dβ, 3dβ–6dβ, respectively. The regio‐ and stereoselectivity in these reactions was determined by ^1^H‐NMR spectroscopic data of the O‐acetylated derivatives.